


Promises

by PassionPhantom



Category: Supernatural
Genre: Alternate Universe, Attempt at Humor, Comedy, Drama, Eventual Fluff, Eventual Relationships, Eventual Romance, Eventual Sex, Family Drama, Gen, Humor, Love, M/M, Multi, Other, Romance, Romantic Comedy
Language: English
Status: In-Progress
Published: 2016-12-04
Updated: 2016-12-30
Packaged: 2018-09-06 11:27:24
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 3
Words: 8,397
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8748841
Author URL: https://archiveofourown.org/users/PassionPhantom/pseuds/PassionPhantom
Summary: ****WILL RETURN TO THIS FIC WHEN OTHER WIPs ARE DONE****In this AU series, The Winchester’s, a hard-working family, can never seem to catch a break in reality.Though with a wild bet on a game of pool and some luck they may have a chance at a real vacation! And with this splendid opportunity, young Dean Winchester will finally be able to do something that has been on his heart for ages. With the support of his immediate family and friends Dean may have the chance to plan the perfect proposal to marry his beloved, Castiel.But will everything go smoothly with the vacation and the proposal? Or will Dean's outrageous family find a way to ruin the surprise?





	1. A Night of Good Fortune

**Author's Note:**

> Hey guys, this will be my first BIG series to post here ( I usually do one shots. So there maybe some mistakes here and there because i am basically an army of one writing this) but I hope you all love this and enjoy it. :)

It was a night of good luck and fortune when Dean and his father John visited the neighborhood bar. They needed some father-son time and Dean had a few things on his mind that he wanted to mention. While ordering their drinks and making small talk Dean finally worked up the courage to say what he needed to speak on. Though before he could actually begin John Winchester suddenly clapped his hands and suggested they go play pool.

All because of some loud mouth drunk who was bragging about how good at it he was and he carried on for quite some time. Honestly both Dean and his father were sick of hearing about it. Knowing that his father was a master at pool and Dean being the once crowned prince of hustling, the two stood up to go crush the guy. Still Dean hoped it would be one solid game and he could get back to what he wanted to say.

“Hey there fella, how bout you say its time to put your skills to the test.” John said as he and Dean stepped up.

“What you got to bet on it?” The man said. “Obviously nothing because you and the kid here look like you live in a gutter.” The drunk turned to a few of his buddies who were close by to receive high fives. “Who still wears flannel anyway?” The man said causing everyone with him to laugh at the two Winchesters.

“Oh hell no,” Dean said under his breath and John nudged his shoulder.

“No worries son, we’re about to squash this guy.” John began to point out to Dean the hints and clues about the man. Things like his attitude despite the drunkenness and the mysterious envelop left idly on the pool table alone. The drunk was a bona fide idiot, talking loudly now about how rich he was and how his life was awesome. It was annoying. Though John and Dean saw the advantage.

“The envelope must be full of cash or something. Especially if the fool is loaded like he says.” John whispered to his son. “Hell, we could literally just grab it and he wouldn’t even notice.”

Dean shrugged and took a step, figuring if the man is so rich then he wouldn’t miss whatever was in that envelop. But John stopped him.

“No no, we’re going to win it fair and square, son. Winchester’s don’t steal.”  
Dean blinked hard after hearing that flat ass lie from his father.

“So what you guys got to bet on ten plane tickets to Hawaii?” One of the guys from the crowd shouted at the two Winchesters.

That’s when John and Dean’s eyes shot wide the hell open.

“Whoa what!” John lost his mind for a second and Dean nearly dropped to the floor…it had been weeks of Dean’s mother, Mary, complaining to John about how they needed a vacation. John continuously promised her that one day they would go somewhere really nice. But never did he think about actually going somewhere and not Hawaii the most of all.  
The Winchester’s were a hard working family indeed but they never actually caught a break in reality. Something was always occurring that would hold the family back from what they truly needed. Money certainly was an issue. Though now here was a chance! To finally achieve something despite the odds or the fact that a drunken man was betting away his own families tickets.

“Dad we have to kick his ass.” Dean said quickly.  
“I KNOW.” John said through his teeth. His mind was racing with all the possibilities of actually winning. “Don’t worry we got this, we got this!”

“Okay man we may not have all the money in the world like yourself,” John Winchester began, “But what I do have is a classic 1967 Chevy Impala in mint condition.” He pointed directly out the window toward “Baby” in parking lot.

Dean tilted his head back and sucked his teeth…. It was another bold ass lie. The car was not in mint condition at all. Not only from the scratches and dents along with years of more wear and tear. But because Dean and his boyfriend, Cas, had just fucked in the back seat last night…and they came everywhere… But that was something Dean was going to keep to himself. And luckily he and Cas went to the car wash immediately afterward to get rid of the evidence. Dean even added in a wax so Dad wouldn’t be too suspenseful. Now, Dean realized all the effort it might actually be worth it.

“Oh shit! A Chevy Impala from 19-what! Fuck outta here! I love that car! I’ve been trying to get that shit for ages but I can’t find one in perfect condition, oh shit!” The rich drunk said very enthusiastically. “Okay okay! The tickets to Hawaii all for that car! Hell I’ll even throw in my wedding ring for it just to show how serious I am!”

That’s when it became too much for Dean….  
‘My God, what is this guy doing????’ the thought snapped in Deans brain with a pop while John’s smile grew wickedly large.

The silly man sipped on his eighth-ish beer and slammed it on the pool table. Dean stood still. Frozen. Watching as the man removed his diamond-studded band off his finger and placed it on the edge of the table next to the white envelope. It was small…beautiful…perfect. Too perfect.

 

“Hey, maybe we shouldn’t do this.” Dean said to his father…John nodded.

“You're right son…. but think about that vacation though. Your mother will finally stop nagging.” John’s eyebrows were so high up that they could touch his hairline. Now the idea of going on a real vacation…for free was so tempting that Dean’s mouth salivated. He swallowed immediately but John noticed.

“Heyyy I saw that! We’re doing this.” John stepped forward and grabbed a pool stick.  
“You’re a bad influence, old man.” Dean muttered under a grin. Still feeling uneasy though.

John smiled and turned his attention over to the rich drunk.

“Alright, if you’re willing to bet all that shit there for one but fine ass classic car.” John snickered. “Then I’m down.”

“Alright!” The man agreed to the bet.

The older Winchester prepared the pool table, racking the balls, while the loud mouth finished his drink…. ordering another one.

Dean circled around the table to get a good view just as everyone in the bar began to crowd around to see what the hell was going on. Only a small amount of intelligent people began to beg the drunken guy, who was named Bernie, to not gamble away his possessions. Still Bernie must not have been a town favorite because no one really stepped up to actually stop the game.

“I’m not about to lose to some old guy and his loser kid alright! I’ve been doing this for years anyway! I never lose!” Bernie shouted pointing his pool stick at the people he knew.

“Dad?” Dean said. “Dad...You sure about this?” Dean asked again. Any other time he would have hustled the guy over but this was too crazy. The guy was completely out of his mind.

“Don’t question it, boy just watch the master work.” John chuckled as the game began.

As the young drunken man stepped forward, he hit a ball swiftly. Confidently, Bernie swaggered around the table without a second thought or doubt. But it was the eight ball that was hit and it was pocketed in such a fast motion that if you blinked you would have missed it. The other balls remained on the table so everyone could see what happened. Bernie’s friends were struck with an aggravated shock and began yelling and screaming at him. While some others in the bar collapsed with laughter. All this happened before the guy realized what he had just did.

“Ooooh dude that sucks,” John Winchester grinned while going for the envelope. Dean had snatched the wedding ring before hand and looked at Bernie who was beginning to shout at his friends angrily trying to defend himself for doing something so stupid. John was already out the door when the man turned his attention toward the two of them. Dean began to haul ass behind his father.

“HEY YOU ASSHOLES IT WAS A FOUL!! BRING ME BACK MY SHIT! IT WAS JUST A FOUL!!! IT WASN'T EVEN A FULL GAME!!!” Bernie chased after the two out the bar. But the two Winchesters were fast--which was a surprising thing for John’s age. When Bernie actually caught up to where they were parked, John and Dean were pulling off in their black Chevy Impala.

“Awww man! I really wanted that car.” Bernie said before hopelessly dropping to his knees. And began to come up with excuses to tell his wife about the tickets and the ring...

Part 2

“So why did you grab the ring Dean? It’s not like we actually need that.” John asked as they made their way down the road. “I figured you would show the guy at least a little mercy. Especially with the way you were talking. Ha!”

“Well, maybe he shouldn’t have done all that bragging in the first place if he was going to do something like that,” Dean said, “But Dad that is what I wanted to talk to you about at first.” Dean rolled the ring around between his middle and index finger. It was indeed perfect. “I’m going to ask Castiel to marry me.”

It hit John like a ton of bricks when he realized that what this evening out was for and bad enough the older man was the one driving because Dean’s words nearly made John swerve off the road.

“DAD!” Dean shouted. But John ignored him fixing the car’s position back into the right lane.

“WOW! DEAN, WHY DIDN’T YOU SAY ANYTHING!!!”

‘Why are you so loud?’ Dean thought--- his heart still racing from nearly dying. He looked at his father regretting that he didn’t insist on driving at first.

“Screw the vacation!! Which is an awesome thing don’t get me wrong”--- John continued, “But Dean wow! You’ve been holding that in all night?”

“A month actually…”

“A damn month, and you haven’t asked him yet? Wait… When are you going to ask him?”

“I’m not sure just yet, Dad. My mind had actually been wrapped around getting a ring. A nice one at that. Cas deserves it anyway.”

“Damn straight, all these years and the shit you two have been through Dean, you know he deserves the best. You lucked out with that one. But you know even with a cheap ring Cas would appreciate it regardless, son.”

“Yeah Dad, I wanted something special for him. I mean,” Dean stopped for a second realizing he was sounding cheesy. But he continued, “I think it’s just about time anyway.”

“Damn straight, Dean!” John snapped. Dean was surprised. “How long has it been and not once have you or Castiel brought this up…honestly both of you need your asses kicked.”

“Why!” Dean exclaimed.

“For making us all wait this damn long!” John was shocked Dean would even ask that. “Wait until your mother finds out! It’s gonna be so---“

“Dad, hold on! I don’t want you to tell mom or anyone just yet.” Dean began.

“Why...Oh, I see. You want this to be a big ass surprise, huh?”

“Well I kinda just want it to be at the right moment Dad…” Dean said. “Maybe on this vacation.” He added with a grin.

“Alright! That’s my boy! Like I said We’re finally doing this!!! Just don’t tell your mother about how we got the tickets okay.” John laughed.

“Dad you know she isn’t going to believe us if we lie about.”

“I knooooow.” John groaned. “But hold up, check and see if those are real tickets in there, because if not, we’re driving back to go kick Bernie’s ass.”  
Dean chortled and took a quick look. The tickets were certainly legit. Much to Dean’s surprise who totally was gearing up for a fight.

The two filled the car up with laughter as they pulled up to their house. Sam and his wife Jessica were out for the evening as well while Mary and Castiel were in the kitchen cooking dinner.

Out in the driveway Dean saw Castiel in the window. He was talking with Mary and smiling. His dark hair messy was usual and big eyes were cheerful. Dean smiled then turned to his father and asked, “So we’re telling them about the tickets tonight or what?”

John shrugged, “Hell yeah, might as well let them know…Besides Bobby can hook us up with some ID’s to make it pass security and plus credit cards to pay for shit.” John winked at his son.

“Criminal.” Dean shook his head with a smile. “You’re a bad influence, old man.”

“Shut up.” John grinned. Then added, “ You’ve never complained about it before. But what was the day and time for the trip anyway?”

With a lift of his brow Dean grabbed the envelope off the dashboard and took another look this time for the flight’s departure. Surprised with himself for not seeing it before. When Dean read it his eyes widened.

“Dad…it’s says 7:30… Tomorrow morning.”

The father and son stared at each other.

And in a split second they were rushing out the car and racing to the front door. Bursting into the house screaming their announcement at the top of their lungs. Making Castiel and Mary drop the lasagna they had just made.


	2. A Night of Crazy.

**Summary for the Chapter:**

> Mary Winchester and Castiel have some bonding time and other things happen........ lol

Part 1

“Castiel, how have you been feeling lately sweetheart?” Mary asked after Sam and Jess left out the front door. The two of them were in the kitchen. Mary humming as she tried to figure out what to make and Cas was sitting at the table looking sad. Mary had noticed the young man’s expression while she pulled the frozen lasagna out the freezer. Castiel cocked his head to the side when he saw her. He remembered her telling Sam that she would actually make dinner tonight.  
“I lied.” Mary winked at him. Cas rolled his eyes.  
“Mary I know you can’t cook so I’ll say made it.” He said.  
“Oh hush.” Mary chuckled, “But answer my question…what’s up with you? You seem out of it today….”

Castiel shrugged. 

Cas had actually been having a hard time deep down because things were a little strange with Dean. Who had been quiet a lot these past few weeks. Distant. As if his mind was somewhere else. Always staring off into space and not listening whenever Cas called for him. Cas worried a bit but decided to keep it to himself. 

Though one thing was for certain; their lovemaking had become more intense than ever. The less Dean talked the more rough and eager he’d be. It was like Dean was in a deep need of Cas and just couldn’t voice the things he wanted to say. So in return Cas gave and did everything he could for Dean. Though Cas wouldn’t admit it was becoming…. a bit much.

Last night in particular; Dean woke Cas up at 3am suggesting they go for a ‘little drive.’ But the two never even made it out the driveway as they bent themselves in all kind of shapes in the backseat of the Impala.  
Castiel’s withering legs hitting the door and the back of the front seat while Dean pumped monstrously into him. Whispering to Castiel in his ear how much he ‘loved and needed him.’ And Castiel would have of replied back with his own ‘I love you’s.’ if Dean wasn’t constantly-and harshly- shoving his fingers into Cas’ mouth. 

 

“Cas, Cas?” Mary Winchester’s voice entered Castiel’s mind and stopped his thought process. 

“Yes, Mary!” Cas looked immediately up at the lovely blonde woman trying to hide his own blush. But Mary saw it. 

“Oh my, Castiel whatever you were thinking about had you miles away.” Mary laughed at Cas for minute than finally repeated her original question after seeing the young man become a bit annoyed. 

Castiel sighed, “Its actually been tough, Mary. Dean has been acting strange lately.” 

“Like how?” Mary asked. She didn’t notice any changes in her son but she knew that Castiel of course would. The two were closer then any couple she seen. 

“He doesn’t look me directly in the eye and he is always nervous for some reason. He is even avoiding me when we are around others at times. And when we are alone he is just so much more physical-------Oh my God, What am I saying!” 

“Yeah Cas, I didn’t expect you to go all the way right there with that one, sweetie.” Mary raised a brow and closed the oven after placing the store brought lasagna into it. Coming over to the table she sat across from Cas and gave him a concerned look.

“But you look worried anyway…. and I don’t want you thinking you can’t ever speak with me. So fess up. Just don’t go into detail about you and Dean.”

Castiel laughed away his embarrassment, “I won’t, Mary. But… Your son is driving me insane.”

“Yeah?”

“Yes…. If you think I’m out of it it’s all because of Dean but I won’t push him. I think he will open up in his own time. But I can’t help but wonder what if he has done something that he doesn’t want to tell me. Something wrong.”

“Cas, stop right there.” Mary Winchester held up a hand.  
“But, Mary…” Cas spoke lowly already feeling doubtful.  
“No listen, you said the right thing about giving him time. So that’s what you should do. Don’t let yourself overthink this and cause you more harm than good, you understand?”

“I understand.” Cas looked down. 

“Oh, Cas. Whatever Dean has to say or has on his mind will come out in the right time and moment. Trust me I know from experience so just be patient.” 

Mary reached over the table and kissed the young man on his forehead.  
“Oh, God. Are you serious right now?” Castiel grinned and wiped the kiss away when Mary let go. 

“Hey you know I care about you sweetie! You’re as much as Winchester as anyone else believe it or not! And if you weren’t with Dean I’d think of you as our youngest.”

“Oh okay, Mary, That’s gross.”

“Yeah it is.” Mary laughed. “Forget what I just said.”

“Nope. It’s burned into my brain. I’m basically your son now, Mary…or should I say, Mom.”

“Okay shut up right now.” Mary pointed her finger getting so serious. 

Though it held some truth that Castiel was truly already a Winchester in his own right. He had been friends with Dean since they were kids. Constantly popping by for a visit or even getting into trouble with Dean for the most childish of reasons. But the love really was there.  
John and Mary had taken Castiel into their home after harsh incidents occurred with his own family in the past. And they only ever showed understanding and kindness toward him. How could he be so lucky to have them?  
And how could he ever doubt Dean? Mary was right though. Whatever was going on with him will clear up soon and Cas wouldn’t have needed to worry in the first place. But deep down something just felt different for Castiel that night. 

“Oh Shit!” Mary’s voice broke Cas’ thought process once again as she got up to get the food out the oven. It wasn’t completely burnt but it still wasn’t a pretty sight. Cas got up to help Mary quickly. And with it being unbeknownst to him Cas’ aided his future mother in law with pulling the nearly ruined meal out the oven.

“You still want to tell Sam and Jess that you made this!” Mary laughed.  
“No no no! This is all you.” Cas chuckled. 

Right when they were just about to set the lasagna on the stovetop, Dean and John busted through the front door screaming about a bet and how they had plane tickets for a trip to Hawaii bound to depart at 7:30am. The ruckus being so great that Cas and Mary jumped and dropped the food all over the floor. 

Dean and John stared know completely it was their fault and dinner was ruined. But as Dean saw the burnt cheese he laughed afterward,  
“Well hell, at least it wasn’t pie!” 

 

Part 2

“Alright! so we got ten tickets,” John began to explain and Mary’s eyes were large with awe. 

“It’s six of us, Mary, and I say we should get Bobby, Eleanor and their girls to come with us.”

“But John on such short notice do you even think that—“

“I get it! But it's Hawaii they're gonna say yes!” John said.  
Mary’s face stayed straight. Not convinced.  
“Okay well in the end it will be up to them.” John raised his shoulders with a deep shrug and looked his wife square in the eye. 

“But what about that Bernie guy it sounds like he must have been doing that silly thing for a reason….”  
“What reason? he was an idiot that got what was coming to him. But honey, this is a miracle! Don’t you think? Mary you been asking for this all the time, baby. And the opportunity is finally here. We have to do it.”

Mary folded her arms and pursed her lips. She honestly didn’t mind the gambling her husband did from time to time when it was over small amounts of cash. But betting the car?….and winning tickets from a crazy drunk just didn’t sit right with her. 

“Are the tickets fake?” She asked.  
“Nooooo! And we checked!” John answered quickly turning out the envelope to show Mary.  
She looked and saw a confirmation number and the departure and arrival times. They were round trips tickets for the week. Leaving that Monday morning and returning late Friday evening. And it was Sunday evening now…  
This realization made Mary’s mouth tremble as excitement built up inside her. It was a perfect timing to have a vacation since the holiday was coming up and everyone was off work…. If they played their cards right everyone could enjoy themselves. Even Bobby and Ellen if they wanted to come. Mary shook her head in disbelief. 

“Oh my God…this is just too perfect, John.” She began to cry a little. But Mary held back her tears. 

“I know right,” John said softly and came closer to her, kissing her. “But baby we got to move if we want to make it, okay?” 

Mary looked up at her husband believing in him and loving him. The two smiled at on another and spared one more moment to embrace.  
Then Mary said, “You have to give these tickets back.”  
John’s eyes shot open, “WHAT WOMAN?” 

 

Part 3

“So ten plane tickets, huh?” Castiel asked. He and Dean were already packing what they can find in their bedroom upstairs.

“Yeah and if we move fast, we can probably be able to make it in the morning. There’s actually a lot to do though. Like letting Sam and Jessica know about it.” Dean whipped out his phone and started typing as fast as he could. But then he heard the front door slam in the distance and the sound of Sam voicing surprise when Dad began to drop the ball on him.

“Well, that’s done.” Dean said with a chuckle. But his eyebrows furrowed as he heard little more yelling coming from his Dad about Mom…. But Dean ignored and turned his attention toward packing his bag. 

‘It will just be me and Cas if they’re not acting right.’ Dean thought to himself. Planning everything out in his head Dean had even took out two of the tickets to make sure of it. He wanted to give Castiel everything he could. A perfect proposal and an even more perfect wedding. It was like a bug had got into him…first the need for the ring and now Dean needed this vacation to go smoothly.  
‘God help me,’ he prayed in his head….’because I have no idea how this is going to work out. But somehow it will.’ And it was a solid promise he made and something he wasn’t going to give up on.

And so there the two lovers were in the bedroom with nothing but piles of clothes, two luggage and silence between them. Cas with his patient heart and Dean with all his secrets. Castiel fought the urge to say anything. He wanted to follow Mary’s advice but it was annoying. He knew well enough that sometimes Mary wouldn’t do what she’d say herself…she would follow her heart and give her husband, John a good talking to.  
So that’s why Cas decided to speak. 

“Dean…” Cas began and than paused…. Dean hadn’t even looked up.  
“Yes, Castiel?” He said. Castiel was taken aback by the little fact that Dean wouldn’t look up. It wasn’t a big deal….but it felt like one for Cas.  
‘Leave him alone dumbass and let him pack.’ Castiel’s first thoughts were telling him. And so he stepped forward just like a dumbass. 

Right in his step Dean looked up with raised brows. And it gave Cas a bit of a relief to see those bright green eyes.  
“What’s up Cas?” Dean asked. Cas thought for a moment then sighed and replied, 

“Dean…. Baby, you have thought this through, right?”  
“What do you mean?” Dean’s heart thumped. He swore he could feel the ring burning in his pocket.  
“I know it’s a one in a lifetime trip for us but you know—“ Castiel spoke slowly as he allowed himself to steer clear of what he originally wanted to say.

“What are you saying Cas?”  
“Dean…Your scared of flying remember?”

Now Dean wasn’t thinking about that at all. His mind was so wrapped up with planning a decent proposal while on the vacation that not even the idea of being on a plane fazed him. And for a split second Dean wondered if Castiel had kept his mouth shut would he have been fine?  
“Dammit Cas…” Dean started to sweat profusely….

 

Part 4

“Sammy please tell your mother we have to go on this trip!” John was destroyed by his wife’s previous words. “First she bugs me about it for the longest and now she rejects the only chance we have.”

“I just feel like you took advantage of that man somehow. And it’s not fair.” Mary kept her voice firm and arms folded. 

“What? He lost the bet. How is that taking advantage of him?” John said. 

“Well Dad, it does sound a bit iffy with the way Mom puts it.” Young Sam Winchester began to speak.

“Sammy, if your not going to help me then shut up.” John said quickly. “And We’re not going to even have this conversation…. Jessica I hope you’re not on the same team as Sam and Mary.”

“Noooo! I actually think we should go….” Beautiful and sweet Jessica made John smile wide. “It’s a bit sleazy yeah… but the guy screwed up on the bet right?”

“Jessica!” Sam was in shock.

And here the four of them were, at a crossroads with their decision. Should they go and have a good time? Which is well overdue for the Winchester family. Or should they do what is considered humane and give the man, Bernie, back his tickets? The intensity in the living room was growing and it wasn't broken until Cas came down the stairs in a rush. 

“GUYS HELP!!!” He shouted. 

 

“Alright Dean, calm your ass down and just breathe.” Sam gave his older brother a brown paper bag while Castiel toweled away the sweat pooling all over his face and neck. 

“Shit Cas, What the hell!” John turned to the younger man and gave him a stern look. 

“What! I was just making sure he was okay with it.” Cas tried to save himself from the boiling wrath of John Winchester…but nothing was going to help. He was in trouble. 

“I’m surprise enough as it was at the bar and during the ride home when Dean didn’t even bat an eye about flying! Now you just had to go and open your big ass mouth!” John hissed at Cas. 

“I’m soooorry, alright!” Cas groaned and held his hands over his head. Feeling a bit like a child being scolded. He realized Mary was right about everything. Let Dean speak in his own time and he was basically a Winchester anyway.  
“If it’s any conciliation, John, the both of us are completely packed anyway.” Cas added still trying to save himself. 

“Well good.” John said sharply. 

“I actually think this is a sign we shouldn’t even be going in the first place.” Mary pointed out. 

“Oh my God, Mary if you don’t-“ John began then Dean shouted suddenly, 

“NO! WE ARE GOING ON THIS TRIP!!! NO MATTER WHAT!” he stood after his proclamation and then suddenly dropped. Sam and Cas reaching for him before he could hit the floor and setting him back down on the couch. 

“Damn….” John and Mary said at the same time, worried. “Maybe we shouldn’t go…”

Jessica not really caring about Dean’s overly dramatic fear of flights was already on the phone with Bobby Singer and his wife Ellen.  
“Hey you guys, you want to go to Hawaii?” Jessica began telling them everything that was going down at the Winchester house and why everyone was so loud in the background. 

“WHAT! WE ARE ON OUR WAY!!!!” Bobby and Ellen shouted over the phone and hung up before even saying goodbye. Which would be pointless because they were at the Winchester’s door within an hour. Their adult daughters Joanna and Charlie marching in sleepily behind them. Everyone with bags in their hands. 

“If you guys anit going…we’ll take them tickets off ya!” Bobby said immediately after coming in. Hugging John and laughing his head off about the bet. All until he turned and saw Dean, “Damn! what’s up with him?”

“Ask Asstiel here! because he’s the one that just fucked Dean up by bringing up his fear of flights!” John shouted and pointed at an embarrassed Castiel. But Cas decided to ignore them all and turn his attention on helping Dean. 

“Baby, I’m so sorry.” Cas said sweetly and wiped Dean’s brow. Dean pulled Castiel close and whispered in his ear,  
“You owe me so much head for this, Cas.”

Castiel rolled his eyes and groaned but then grinned. Deep down he was glad he didn’t bring up what he really wanted to say back in the bedroom…maybe this whole situation was a good cover up for his original doubt.  
Or maybe this is what Mary meant about making matters worse. Cas felt bad about the idea of not going to Hawaii all because he didn’t shut up. But then Dean spoke,  
“Don’t worry about it Cas, I would’ve freaked out as soon as we had gotten to the airport.” 

Castiel chuckled, “ But we’d be at least there.”

“Oh don’t doubt it we’re going on this trip no matter what. I put our tickets aside just in case these bozo’s decide they want to back out.” 

“OH REALLY! SO WHO DO YOU THINK YOU'RE CALLING A BOZO, DEAN!?” John shouted at his son from across the living room. The two lovers didn’t notice that the room had gone quiet and everyone was listening to them. 

“Yeah! With your sweaty ass!” Sam joined in. “You know what Dad put me down I’m going! Shit I’m not a bozo. HEY MOM YOU’RE ON YOUR OWN NOW!” 

“What! Come on Sammy!” Mary threw her hands in the air still unwilling to admit defeat. 

“Everyone who wants to go to Hawaii raise your hand!” Sam said started and everyone else’s hands shot up. 

“Looks like you’re the only bozo in here, Mary!” John chortled. 

 

By the end of the night the group was settled down, packed and on their way to the airport early the next morning. The only question left to remain will they make it passed security?

**Notes for the Chapter:**

> Find out in chapter 3! Coming Soon! :D


	3. Anything that can go wrong....Will go wrong.

**Summary for the Chapter:**

> The Winchesters make it to the airport to catch their flight to Hawaii. But the other question on everyone's mind is with Dean's intense fear of flying will he and Cas be able to make it through security???

**Notes for the Chapter:**

> This was a tough chapter to write!! I had a terrible writer's block recently but I pushed my way through so i can have something for you guys. So be gentle with me please. lol Enjoy <3

“Okay so we need to split up in two’s to keep them from being too suspicious.” John had announced before everyone hopped out of Bobby Singer’s van. “And be careful to go by the names on your ID’s at the checkpoints. You don’t want them catching on. Alright!”

“Alright!” Everyone agreed sleepily as they got out and made their way into the large airport. Sam and Jessica walking ahead of everyone, Bobby and Ellen together hand in hand talking softly to one another. The sisters, Joanna and Charlie were also casually speaking while trailing behind their parents groggily. Finally Castiel and Dean had got out the van. Only to be stopped by John and Mary.

“Okay you two; hurry up and go first,” Mary said with her husband nodding in agreement.  
“Once they get you out of the way then there shouldn’t be much to worry about especially for everyone else.” John said.  
“And if they ask any questions about why you keep sweating so much, Dean, just tell them your in a hurry and you have to take a shit or something.”  
“Dad!” Dean protested then thought about it for a moment. Cas chuckled and Mary was slightly appalled.  
“Or just tell the truth about your fear to fly.” Mary said. “But be natural with it though. You two are just a couple trying to catch a flight and you so happen to a be little scare that’s all.”  
“Okay we get it! We don’t need a prep talk.” Dean held up a hand. Then he wiped his dry forehead. “You see I’m not even sweating right now. It’s all good.”  
“Well we are outside and the wind is blowing Dean,” Cas smirked and clutched his arms around himself as it was a bit chilly that early morning.  
“Shut up, Cas.” Dean said and stepped away slightly. Cas raised a brow and frowned.  
“Cas, remember this is your fault anyway.” John smirked and suddenly he reached and squeezed Castiel’s shoulder and held it for a second.  
“Take care of my son.” John told Cas.  
There was a certain look in John Winchester’s eye that Castiel caught. As if the older man knew something that Cas didn’t. And there was a feeling in the younger man’s gut that warned him not to ask why.  
‘Maybe this is just him trusting me.’ Cas thought and nodded at John.  
“Yes sir.” He said as John stepped away along with Mary; who ordered the young couple to get ahead of the group again. Dean and Cas followed suit quickly. Eventually running passed the rest of the group.

At 5:30 that morning the airport was full of people boarding early flights for the upcoming holidays and the group rushed to get their boarding passes and bags checked. The lines were long already and tension was growing with irritated TSA guards. Though on the bright side things were moving at a steady pace and nothing else seemed suspicious. Other than the Winchesters and Co. with their fake ID’s. 

“Alright here we go.” Dean whispered to Cas aka Calvin Hudson according to his ID. Which was provided and professionally forged by Bobby Singer himself. Dean was posing as a man named Don Hudson and little did the Dean know that the two names on the tickets were an actual couple as well. And just last night Bernie, the rich drunk, was shouted at by not only his wife and kids; but by also his brother, Don and brother in law, Cal. 

Castiel chuckled nervously at Dean’s comment. Cas was actually worried about being ahead of the group. Unsure if it was a good idea or not but John had made a point about getting Dean out of the way. 

Maybe Dean would be okay or maybe he would eventually freak out again. But no matter Cas was prepared to help Dean by any means necessary. Despite all that Cas knew something was on Dean Winchester’s mind, something that made his eyebrows pull together into a tight knot and made his eyes narrow. Whatever it was Cas swore to be patient and that he would also take care of Dean.

“Are you feeling okay?” Cas asked finally while waiting in line. Wrapping his arm gently around Dean’s and taking his hand in his own.  
“I’m fine…” Dean answered without looking at Cas.

Of course Dean wasn’t actually ok. He was holding up a front while His stomach was actually flipping and turning. Internal screaming filling his head but Dean wasn’t going to admit that to anyone not to the security guards if they find out or even to Cas. He didn’t want to appear weak in any way possible. Still he could feel Castiel’s eyes on him…  
“Don’t worry.” Dean said and finally looked at Cas with a wink. “Like I said this is going to happen.” Cas smiled a bit but then noticed how Dean unhooked his own arm from his. Though he chose not to speak. The two quietly continued to move toward the signs that read TSA.

 

“So you think Dean is going to make it?” Jessica asked Sam while in line only a few feet away from Dean and Cas.  
“Nope…” Sam laughed and received a playful punch from his wife.  
“Oh ye of little faith, Sam!” Jessica chuckled. “But really I think they’ll be okay. Your brother won’t ruin this because of his stupid sweating…or will he?” Jessica’s eyes widened at the sudden thought.  
Sam patted her on the back. “Well if he does then that means more room on the plane for us. Ha-ha!”

 

“Do you think those two are going to be alright?” Mary turned to her husband. John looked up ahead his eyes scanning to spot Dean and Cas.  
“They better.” He said. “Dean and I went through too much to get these tickets.”  
“You didn’t go through anything you practically stole them.” Mary commented under her breath and John shot a dirty glare at her.

Bobby and Ellen were also a few feet away with their daughters close behind. Ellen like Mary and Jess was worried about the boys up ahead and she expressed her concern to Bobby, who replied,  
“Don’t worry Ellen…. If those two idjits screw up then that’s on them…We’re good. We’ll be in Hawaii and on beach relaxing before you know it.” He kissed her on the cheek gently.  
“Alright, Bobby.” Ellen nodded with a smile after receiving the kiss. Then she turned to give her daughters the signal- a simple wave. 

“Looks like everyone is betting against Dean and Cas” Joanna told Charlie.  
“Do you think Dean will get caught because of his stupid phobia?” 

“No.” Charlie rolled her eyes and shrugged. “Dean’s going to be fine. He’ll pull through. He’s tough enough not to crack under pressure. So I think everyone else needs to chill.”

“True that…” Jo agreed.  


“Alright ‘Mr. Hudson’ you’re all set.” One of the guards said after checking Dean’s boarding pass and ID. Dean nodded and stepped forward to put his duffle bag on the belt to be scanned and to go through the metal detector. But in a split second as he stepped through, the machine went off loudly. 

“Oh shit….” Everyone of the group of ten somehow managed to say collectively even while separated. Dean’s eyes shot wide open and his heart skipped more than just a beat. He looked back at Castiel desperately now all of a sudden and his expression made Cas ache. ‘Stay calm, baby’ Cas thought. Praying that Dean could somehow read his mind. ‘Relax… relax. Don’t sweat so much….”  
Sweat started to form all around Dean’s face.  
“Crap.” Cas said lowly as he noticed. 

“Sir do you have any keys, lose change or even jewelry on your person?” The hefty security guard asked stepping toward Dean. Dean shook his head struggling for a moment to think why the hell would the detector go off on him of all the people in the airport; it just had to be him.  
Then hit Dean like a ton of bricks.  
‘Oh shit! The wedding ring!!’ Dean screamed in the inside of his head. His eyes couldn’t get any larger then they already were and he fidgeted nervously as the male guard gave him a pat down. 

“Sir, if you have something in your pocket. Please take it out.” The guard said. Dean gulped hard looking over his shoulder at Castiel who stared back intensely. Dean’s mind raced,  
‘Oh my God he is going to see the ring! This cant be happening! Oh God please!’ his heart pounded and everything seemed to slow down for a second. The surprise was about to be ruined.

But just at that moment an elderly woman bumps into Cas making him trip over and all the material in her carry on bag to fall out. Thankful, Dean saw his chance and turned back to the guard.  
“Oh, it’s just my ring.” Dean took it the ring out and put it on quickly- without thinking. The guard stared at Dean for moment then over to the dark haired young man, who was getting up and kindly helping the old woman with her belongings.

“Oh okay,” The guard said after putting it all together. “Well make sure to put that in the bin with your other personal items next time sir.” He said and then let Dean through.  
“Yeah I’ll make sure of that. I wasn’t even thinking about it.” Dean nodded.

“Just be careful, sir. Besides you two make a lovely couple and you shouldn’t be ashamed to wear your rings in public anyway.” The guard added. Dean’s brows pulled together as he caught the comment. Walking away from the guard Dean held a small smile but he was silently dying to get the ring off his finger and into his bag. Which he got off the rotating belt quickly along with his shoes. Dean felt like an idiot for not putting it away before. It was just so much commotion at the house and the rush to the airport Dean simply forgot.  
After putting on his shoes and grabbing the bag Dean snatched the ring off swiftly and stuffed it into the side pouch of his inside duffle bag. Zipping it tight. Just in time as Cas made his way out the detector smoothly and received a quick pat down.  
“I hope you and your husband have a wonderful day.” The guard said to Castiel before stepped to the side to grab his own bag. He was left dumbfounded by the comment.  
“What—okay thanks.” Cas said with eyebrows lifted. Moving quickly Cas went over to get his belongings and to catch up with Dean. “Hey! Why did the metal detector go off? Are you okay?” Cas eyes were full of concern and Dean couldn’t concentrate enough to look into him.  
“Oh it was nothing, baby, just my keys.” Dean lied.  
“Oh… oh okay. That silly but guess what! That guard thinks that we’re married.” Cas chuckled. His grin stretching from ear to ear.  
“Whatttt! I wonder where he got that from!” Dean rolled his eyes and looked up to see the hefty blond guard smiling at them.  
“Aww that would actually be kind of sweet. Just imagine…” Castiel went on and on for a moment but then turned to see Dean walking away very fast. The horror of the surprise nearly being ruined written was all over his face. And now Cas was talking about it. It was too much.  
“Hey, wait up!” Cas rushed to catch up with him. 

 

“So what in the hell happened?” everyone asked immediately when they all regrouped at their assigned gate after making it through security.  
“It was just my keys guys. Its no big deal.” Dean replied and waving them all away trying to change the subject quickly. Knowing full well that his family would start to make fun of him all too soon “Its too early in the morning for all this BS anyway.”  
“Well we’re glad you made it through anyway.” Joanna said while taking her seat.  
“Thank you Jo.” Dean smiled feeling good to have another person his team. But then Sammy said,  
“We’re still betting to see if you’re going to piss yourself during the flight though.” He laughed hysterically and Dean shot his brother a dirty look but then chose to ignore him. Turning his attention toward their father. There was a more pressing matter that Dean had to attend to but he swore to get Sammy back soon. 

“Hey, Dad you got a second?” Dean asked.  
“Sure kid.” John rose out of his chair and put down the magazine he was reading. The two of them went for a walk and Sam was the only one to notice something was up...

Cas had already taken his seat and placed his bag on the chair next to him to save for Dean. He couldn’t help but think of how Dean walked away so quickly like that. Or how he kept a distance from him while they were in line. This made him a little sick with worry deep down. ‘It wasn’t a big deal right?’ Cas thought. ‘It’s nothing. I shouldn’t even worry about it…. last night was such a close call that I should really be more careful. But…’  
He needed to talk about it so he quickly turned to Mary.  
“Yes.”  
“Last night I… last night I almost broke the first rule of fight club.”  
“What, Cas?” Mary was confused for a moment. Then it hit her.  
“Boy!” She slapped Cas’ forearm with the magazine in her hand.  
“Ow, Mary I said almost!” Cas complained.  
“Is that the reason why Dean’s fear of flights came up?” Mary was right on the money.  
“Well, You see what happened was-” Castiel began but received another whack from Mary before he could think of a lie. “Ow! Mary please stop that! I was only going to mention how he hadn’t been looking at me directly but I thought of you and what you said… So I changed the subject faster then Usain Bolt. And the Dean’s phobia is the first thing that came out my mouth!”

Mary shook her head; “Well you’re going to have to be the one to keep him calm during this flight. You know it’s going to be like 8 to 9 hours Cas.”

Cas laughed, “Oh….” Then he became nervous, “shit.”

 

“So what’s up son?” John asked turning to his son as they walked throughout the airport.  
“Dad…I almost couldn’t get passed security because of the ring!” Dean explained all what happened.  
“Geez, really!” John laughed. “What kind of metal is in that thing? Ha-ha”  
“Its not funny, Cas could of seen it. He almost did!”  
“Wow! Dean You must have been a mess….” John couldn’t help but laugh but he straightened up his expression when he saw how seriously distraught his son was.  
“Oh Dean don’t worry I wont laugh. I have something for you anyway.” John reached into his pocket and pulled out a tiny black box. “We can’t have you stupidly walking around with something that valuable unprotected. So I got this for you before leaving the house. It’s nothing special… just the same one I presented to your mother.”  
Dean took the box slowly. “Wow. Thanks Dad.” He reached into his duffle bag for the ring and then placed it inside the little black box. It took a second for the width of it to fit inside but it went inside and the box clasped close completely. Nearly perfect. 

It felt official. Almost the right time. But Dean didn’t want to end up proposing in an airport. It had been a month, a damn month of worrying about the right time and how it should be. But Dean knew it one morning when he woke up and saw Castiel sleeping soundly that it was time. After all these years, the good and the bad Dean knew in his heart that Cas was the one. He just needed to make it final for him.  
“Dean, you alright son?” John asked.  
“Yeah, I’m good.” Dean said…wiping a small single tear. “Just got something in my eye.”

“Uh huh, put that thing away and come on you big mush ball. The flight is going to be boarding soon.” John nudged Dean’s arm playfully. The young man did what his father told him quickly and the two turned to go back to the group.  


The boarding for the early first class flight was settled and everyone was in their seats already dozing off into deep a sleep before the plane was ready for take off. Castiel looked around to make sure the coast was extra clear as he had just came up with a bright idea.  
“Okay Dean this is it.” He smiled and Dean looked at him.  
“What do you mean baby?” Dean had asked as Castiel stood and grabbed his bag pulling out a blanket and a pair of headphones. Than settled back down into his seat.  
“I’m going to take care of you.” Cas whispered with a smile and gave him a small kiss.  
“Don’t worry about me baby.” Dean said. “I think I’ll be fine.” But Cas had already made sure he was well prepared. He placed the pair of headphones on Dean’s head and threw a blanket over their bodies and even asked the flight attendant for two pillows. 

“You know having all these things is going to make me sweat even more.” Dean chuckled and swallowed hard anticipating what his lover was planning to do to him under the blanket.  
“I’m going to make sure you’re as relaxed as possible and don’t worry about this,” Cas gestured to the blanket, “We’re only going to need it for a second Dean.” Castiel held a big smile and gave Dean a naughty wink.

**Notes for the Chapter:**

> Phew! I'm Glad that worked out. Find out the 'tactics' Castiel uses in order to keep Dean calm during the flight's take off in chapter 4! Coming Soon! ( ^ . ^)


End file.
